Synthesis and electrochemical redox properties of arylated p-benzoquinones, naphthoquinones and alkylamidoalkyl-p-benzoquinones

Quinones are known to be medicinally active compounds, where the activity resides both in the oxidative power of the molecules as well as the antioxidant behavior of the respective hydroquinones. In vivo targets of the compounds may be diverse biomolecules, including proteins, which may provide a highly polar environment for the benzoquinones at the reactive site. Against this background, a number of arylated p-benzoquinones, naphthoquinones and a series of alkylamidoalkyl-p-benzoquinones have been synthesized, and their redox behavior has been studied in the in ionic liquid, 1-butyl-3-methylimidazolium tetrafluoroborate, using a gold microelectrode. Diffusional coefficients and solvodynamic radii of the neutral species have been calculated for all quinone derivatives.